Details

Autor(en) / Beteiligte

• Greengrass, Colin W
• Hoople, David W. T
• Street, Stephen D. A
• Hamilton, Fiona
• Marriott, Michael S
• Bordner, Jon
• Dalgleish, Angus G
• Mitsuya, Hiroaki
• Broder, Samuel

Titel

1-(3-Cyano-2,3-dideoxy-.beta.-D-erythro-pentofuranosyl)thymine (cyanothymidine): synthesis and antiviral evaluation against human immunodeficiency virus

Ist Teil von

• Journal of medicinal chemistry, 1989-03, Vol.32 (3), p.618-622

Ort / Verlag

Washington, DC: American Chemical Society

Erscheinungsjahr

1989

Quelle

MEDLINE

Beschreibungen/Notizen

• 1-(3-Cyano-2,3-dideoxy-beta-D-erythro-pentofuranosyl)thymine (cyanothymidine) (3a) has been prepared by an unambiguous route starting from D-xylose. The relative and absolute stereochemistry of 3a and its anomeric isomer 9 have been confirmed by NOE experiments and by X-ray diffraction analysis. In antiviral tests vs HIV 3a was shown to be inactive, a surprising result in view of a preliminary disclosure claiming potent anti-HIV activity. The activity previously assigned to 3a is believed to be due to contamination of that sample with the known antiviral nucleoside analogue 5b.